ChemInform Abstract: New Syntheses of 2‐Acylbenzofurans, 2‐Acylindoles, 2‐Indolylcarboxylates, and 2‐Quinolones by Intramolecular Wittig Reaction.

Abstract

The phosphonium salts (I) react with the acid chlorides (II) immediately to give the benzofurans (III) (the intermediate 2‐(α‐ketoacyloxy) salts are not isolated).

Synthesis, Biological Evaluation, and Structure−Activity Relationships of 3-Acylindole-2-carboxylic Acids as Inhibitors of the Cytosolic Phospholipase A2

“…33 Ethyl (3-Octadecanoylindol-2-yl)acetate (7). To the refluxed solution of N,N-dimethyloctadecanamide (374 mg, 1.2 mmol) and POCl3 (153 mg, 1 mmol) in dry benzene (10 mL) was added in one portion the solution of ethyl (indol-2-yl)acetate ( 6) 49 (203 mg, 0.4 mmol) in dry benzene (3 mL). After 3 h an aqueous sodium acetate (1 g/4 mL) was added, and refluxing was continued for an additional 15 min with vigorous stirring.…”

Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors

“…A mixture of 2-hydroxybenzylalcohol (16.27 mmol) and PPh 3 •HBr (16.27 mmol) in CH 3 CN (40 mL) was stirred under reflux for 2 h. The solid formed was filtered and washed with CH 3 CN to give the desired compounds IIa-IIc [20,24,25].…”

“…The desired Wittig reagent was readily prepared from the conveniently substituted 2-hydroxybenzyl alcohol Ia-c and triphenylphosphine hydrobromide (PPh 3 •HBr) [20][21][22][23]. The key step for the formation of the benzofuran moiety was achieved by an intramolecular reaction between 2-hydroxybenzyltriphosphonium salts IIa-c [20,24,25], and the appropriate benzoylchloride.…”

Palladium-Catalyzed Regioselective 2-Carbethoxyethylation of 1H– Indoles By C-H Activation: One-Step Synthesis of Ethyl 2-(1H-Indol-2-Yl) Acetates

“…Accordingly, the literature describes several preparations of ethyl 2-(1H-indol-2-yl) acetates. For example, Capuano et al demonstrated that the intramolecular Wittig reaction of 2-[(ω-alkoxycarbonylacyl) amino] benzyltri-phenylphosphonium salts produced 2-(1H-indol-2-yl)-acetate with a 78% yield [21]. Furthermore, Moody et al reported that reductive cyclisation of the ethyl 4-(2-nitropheny)-acetoacetate using titanium(III) chloride in aqueous acetone gave 2-(1H-indol-2-yl) acetate with a 75% yield [22].…”